DIY: There are basic guidelines to red: Blue-based crimsons flatter cool skin tones, while orange-red hues look best against warm skin tones. But most importantly, says McGrath, "Don't torture yourself over selecting a shade. I do 60 shows with one shade, and every model looks amazing." Start by carefully tracing lips with a matching liner to "contour and define," Kendal says, and apply the lipstick using a brush for precision.